Here's another one instead. If you handed an IPad 2 to the person who developed the original IBM computer would it even be comprehensible to the original developers?
Other than getting faster and smaller computers on a fundamental level have are not too much different today than they were 30 years ago, IBM developers operating in the 70s likely figured they sooner or later what transistor technology would be capable of they just knew that it wasn't at that point right now. So, yeah, an IBM developer from the 1970s would likely be able to understand a modernday iPad.
However to go more extreme the first iPad or even the first IBM computers would be utter magic to someone living in the 1920s or 30s whose computer knwoledge revolves around machines fucntioning off vacuum tubes and machines that occupy the space of entire rooms to the most basic of tasks right now that are something we take for granted out of a simple pocket calculator.
A person living in 1930 would look at a printed circuit board filled with these strange paths of gold and copper paths, these odd little black boxes, he'd have no clue what was going on with it and wouldn't even know how to even start to re-engineer it or reproduce it. This was the problem in the TNG episode "A Matter of Time" where a 22nd century inventor intends to take 24th century back home to "invent" it. Technology that's two centuries beyond anything he's ever seen, such a concept is ridiculous. A person from 1811 would be at a loss when looking at a modern day version of something he uses everyday. Could he understand how a fully automatic machine gun works that can fire 300 rounds a second when he's used to a simple six-shooter that jams half the time between cocking it?
In my opinion it'd be impossible for someone to comprehend a piece of technology that's more than a decade beyond their years, and while it may be possible for them to figure things out and how it works then they have to get into the world of reproducing it and we could make a valid "chicken and the egg" argument that for a device to built whatever is building it has to be almost as sophisticated. You're not going to reproduce microchips on a machine that's running off vacuum tubes.